


Dean Has Been to Hell and He Can't Take a Period

by The_Most_Obvious_Sherlockian



Category: Supernatural
Genre: Angel Castiel, Car Impala, Car Sex, Confused Castiel, Dean Hates Witches, F/M, Female Dean Winchester, Gender or Sex Swap, Horrified Sam, Impala Sex, Physically Hurt Sam Winchester, Surprise Kissing, Vomiting, Witches
Language: English
Status: Completed
Published: 2015-05-25
Updated: 2015-05-25
Packaged: 2018-03-31 22:02:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,816
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3994492
Author URL: https://archiveofourown.org/users/The_Most_Obvious_Sherlockian/pseuds/The_Most_Obvious_Sherlockian
Summary: <blockquote class="userstuff">
              <p>Sam hurt his ankle on a hunt so Dean goes out on his own, assuming he can handle one silly witch. He's not wrong, but he walks away a changed man. Or... woman.</p>
            </blockquote>





	Dean Has Been to Hell and He Can't Take a Period

Dean threw the remote controller on the bed Sam was lying on. Sam smiled up at him uncertainly.

"Are you sure you wanna do this, Dean?" he asked, "I mean, I should be able to walk fine in a few days."

"Nah, I'm good. Nothin' special, just your everyday witch. I don't want you huntin' on a bum ankle. Knowin' you, you'd slip and break your neck. I'm not really feelin' like makin' another demon deal. Check back next week," he ruffled Sam's hair like he did when they were kids.

Sam chuckled, "Okay Dean. But if you come back with an ass head or somethin'-"

Dean scoffed before Sam could finish, not catching the Shakespeare reference, "You want me to pick up some soup?" he mocked.

Sam rolled his eyes and picked up the remote, "Get outa here!"

Dean gave Sam his best 'mom' face, "Not to much porn, now. If you make a mess, make sure you clean it up before I get back. I don't want to see that shit-"

"Dean!" Sam exclaimed.

Dean laughed and opened the hotel door, "See ya in a few Sammy. Don't you walk on that ankle." And then he was gone.

Sam flicked through channels, and eventually settled on a Lord of the Rings marathon, about ten minutes into The Fellowship of the Ring. By the time Sam was about halfway

through The Two Towers, he heard the door rattle. He reached beside him and grasped his gun, but as expected, it was only his brother.

Dean walked through the door, looked at the TV, and scoffed, "Nerd," he said, and then coughed. 

Sam let go of his gun and put the TV on mute.

"That bitch hit me with her green humbo jumbo crap," Dean said, his voice hoarse. "Can't talk right. Don't think there's any serious damage," he coughed again. "Already getting better."

"Dammit Dean!" Sam exclaimed, sitting on the bed so his feet were touching the ground, "I knew you shouldn't have gone alone!"

"Shut up!" Dean said, his voice getting higher at 'up'. Higher than usual... "I'm fine!" He dumped his dufflebag on the bed. "I'm gonna go to the store, I just wanted to dump my extra witch killing..." he waved his hand absently at the bag. "You want anything?" 

Sam just shook his head, "Don't get... cursed or anything."

"I'm not," he coughed, "cursed!" And he walked back out the door.

Sam raised his eyebrows and sighed. "Well," he said under his breath, "Whatever it is, he's had worse." He picked up the remote again and un-muted the TV. This time, it was only half an hour before the door rattled. Sam reached beside him again, but didn't actually touch the gun. Until the door opened, that it. It wasn't Dean, but an average height, extremely attractive, green eyed, woman with just above shoulder length sandy-brown hair who walked through the door with a bag of groceries. 

In an instant, Sam was holding his gun. It was cocked and pointed at the woman, ready to fire.

"Who the hell are you?" he demanded.

"Sammy c'mon it's-" she furrowed her brow and coughed, as if she was confused by her voice, "me," she finished weakly. She shook her head and began to walk forward but was stopped by Sam.

"Stop right there!" he full on yelled, his gun following her.

"Whoa! Dude!" She was wearing an ill fitting red and black plaid flannel, with an equally ill fitting black t-shirt beneath it. Her jeans seemed way too big. "What the hell man- what is wrong with my voice? I sound like a-" she stopped when she caught her reflection in the mirror she was standing by. All her attention was then off Sam- and the gun- and on the reflection.

"Holy shit!" she almost screamed after she carelessly dropped the bag of groceries on the floor. A cherry pie fell out of the bag.

"Dean?" Sam asked skeptically.

"Oh my God, Sammy," she, shamelessly, grabbed her boobs. Then, she turned around, hands still on her breasts and looked at Sam, wide-eyed, "Sam I have boobs!" she yelled.

 _Yep_ , Sam thought, _that's Dean._  Then, after a few seconds, _My brother is a woman._

"What the hell happened to you?" Sam asked, not sure whether to laugh or be extremely worried.

Her eyes remained wide open, "I have no idea! Maybe it's whatever that witch did to me!" her hands were still on her boobs. She gasped audibly and ran her hands through her hair, "God that is so weird!"

Sam raised his eyebrows, his gun still pointing at her.

"Dude I have /got/ to check this out!" she exclaimed, practically running towards the bathroom.

"Don't... I don't know... do anything weird," Sam called after her, the point of his gun had followed her until she ran into the bathroom but now, he just felt ridiculous, so he set it back on the nightstand. He made sure he had a silver knife in his jacket.

"No promises," she yelled back, and after a few seconds, "Holy shit!"

Sam gritted his teeth, wishing his brother/sister, if that was even what he/she was, could be a little quieter about his/her discoveries. Especially after they apparently got more adventurous, and a pleasured moan was heard through the bathroom wall. Sam's eyes widened, "Dean!" he yelled. He stood, avoiding putting excessive amounts of weight on his injured ankle, and hobbled over to the bathroom door. "Dean quit, I can hear you!"

"Mmm Sammy, I don't know if I want to."

Sam really started to get freaked out then, and he hammered on the bathroom door, "Dean Winchester get your ass out here."

There was silence on the other side of the door.

"I hope you're using this time to put any clothes you may have taken off... back on," Sam said. He couldn't remember ever being more uncomfortable.

Slowly, the door opened to reveal a thankfully fully clothed woman. Her hair was sticking out in all directions, unlike when she had entered the room.

"Sam, am I a lesbian?"

Sam furrowed his brow in equal parts confusion and annoyance, "How should I know?" he demanded. "And speaking of things I don't know, how do I know that this is really... you?"

"It's not that I have anything against being a lesbian I mean-" she chuckled, "God knows I love lesbians, but it's just weird to think of myself as gay after all this time trying to convince people I'm not."

"Dean, c'mon. It's not like I can just do the normal tests. I mean- I can, but it's no help, you could be a completely different person just pretending to be a female version on my brother-"

"Sam! Sam!" she interrupted, putting one of her hands in the air for added effect. "It's me. Sammy, it's me," she pulled the Impala keys out of her jeans pocket, "Would I give these up without a fight?"

Sam raised his eyebrows, "Sorry, but I'm gonna need more than your car keys."

"Okay, you know what? I am surprisingly horny right now, so I'm gonna go out and get me some- don't worry, I'll take my gun- I'll be back in like- I don't know, a few hours," Dean pushed past Sam and started walking towards the door, "so you figure out how you want me to prove I'm me, and I'll just... go find me some hot chicks," she stopped before she got to the door, though, and looked at herself in the mirror.

"Do we have anything more... I dunno, flattering?" she asked, wrinkling her nose at the reflection.

"For you?" Sam asked, taking a few steps towards her.

"You're right," Dean said, honestly ignoring Sam, "I'm gonna have to pick up something new."

"Dean, you are not wasting money on clothes! Since when do you care what you look like anyway?"

Dean turned to face Sam, "Oh, Sammy. I always care what I look like," she assured him, "The whole flannel, t-shirt, jeans thing? I look hot. Well, dude me looks hot. I'm sure chick me will too. I just need to get somethin' that fits."

"Seriously?"

"How am I supposed to get laid lookin' like this? Sammy?" she demanded, gesturing at her outfit, "The flannel can stay, I just need to get a new shirt and some jeans that fit," she turned back around and looked at herself in the mirror again, "And some new underwear 'cause these boxers... not hot," she did a little jump and grasped her boobs again when she landed, "And a bra would be nice."

Sam took a deep breath and looked at the ceiling, determined to look anywhere but at his... sister.

"I'm not gonna go to Victoria's Secret or anything," Dean assured her brother, "I just want to look... well not like a homeless chick."

"Why are you so cool with this, Dean? I would think you'd be pissed if you got... somehow turned into a chick?"

Dean turned around again, "Hey, man, what's wrong with bein' a chick?" she laughed in a way that Sam could picture his BROTHER doing exactly the same thing, "I can look at boobs whenever I want!"

Sam sighed. Well, if that woman wasn't actually Dean, she was a great actress. And she defiantly had spent time with him, "Whatever. Do what you want."

"You gonna keep watching the nerd-a-thon?" she asked, raising her eyebrows.

Sam rolled his eyes, "Yeah, sure."

"Okay. Cool. Just- uh... stay off that ankle," she said with what came across as genuine concern.

"Right."

"And I don't need to tell you about porn-"

"Whoa!" Sam yelled. "That is so much weirder coming from... chick you!"

Dean chuckled, "It's still me, Sammy. Still your big brother." and with that, she walked out the door, picking up a key on the way.

As soon as Sam heard the Impala roar away, he hobbled over to his bed. His gun and his phone were still on the nightstand. He picked up his phone and scrolled through his contacts until he found Cas. After a moment's hesitation, he hit 'call'.

"Hello Sam," came Cas's gruff voice after two rings. 

"Hey, Cas, I think I need your help."

"What's wrong?" he asked, worry evident in his voice.

"It's Dean-"

"What happened, Sam? Where are you?"

"I'm... we're in California hunting a witch. Well we were hunting a witch, I hurt my ankle and Dean killed her. I guess he got hit with... some sort of spell and now he's... well he changed. Physically."

"Is he there? Put him on the phone."

"No, he just went out. I think it'd be good if you came here. I need help makin' sure it's really him. And fixing him."

"Where are you?"

"I'm at a hotel in Santa Cruz. I'll text you the address."

"I'm a few hours away. I'll be there soon." Cas hung up.

After he texted Cas the address of the hotel, Sam found himself once again with nothing to do. He turned the volume back up on the TV, and collapsed on the bed. 

"I should do some research," Sam mumbled. He leaned against the headboard with pillows between his back and the wood. He looked around the room and sighed. His computer was all the way across the room. 

"Or not." So he just watched the movie. 

Cas got to the hotel before Dean, after The Return of the Kind had ended and Sam was a few episodes into a marathon of Bones (it was on the same channel). He knocked on the door, but opened it on his own before Sam could even get up.

"I forgot, you hurt yourself," Cas said, walking to the bed. He put two fingers on Sam's forehead and closed his eyes. Sam's ankle immediately stopped aching. "I'm sorry I'm late. I typed the address into the GPS on my phone, but it seemed like it tried to kill me so I decided to try to find it by myself."

Sam chuckled and stood on his newly healed leg. "Well I'm glad you made it."

"So, what's wrong with Dean?" Cas asked, as usual, not wasting any time on pleasant conversation and getting straight to the point.

"Well-" Sam was cut off by someone new sticking the key card in the door, "See for yourself," he said quickly.

"Sammy, you're gonna hate me," Dean started as she walked through the door, "Her name was 'Jess,'" she looked up at Sam, then her eyes skimmed over Cas, "Oh, hey Cas," she said quickly, dropping the hotel and car keys on the little table. Then, as if she just realized what she'd seen, she looked back up at the angel, "Oh hello Cas," she said, a mischievous smile growing on her face. She walked up to the extremely confused Castiel, a little closer than usual. "Aren't you lookin'... delicious?"

"Dean, what the hell are you doing?" Sam demanded. Dean released the terrified angel from her penetrating stare and turned towards Sam. 

For the first time, both the man and the angel saw what she was wearing. She had Dean's red and black flannel still, it was rolled up to the elbows and unbuttoned. Underneath that, she had on what appeared to be a black tank top which clung to her curves and showed a generous amount of cleavage. She had collected a new pair of dark blue jeans as well. They were tight about to the mid-shins where they were revealed to be boot-cut, but they still showed off the elegant shape of her muscular, long, now straight legs. She hadn't purchased new shoes. She had, however, purchased makeup. And somehow applied it. Her eyelashes were coated in a rather generous layer of mascara and eyeliner- well it lined her eyes. Her eye-shadow matched her eyes.

She raised one perfectly arched eyebrow, "I've decided to go by Deana," she said simply.

"No," Sam said, "You're going to go by Dean. And Cas is gonna check you out and make sure it's you. He'll fix you. He'll get your Y chromosome back."

Deana shifted her attention back to Cas, "I don't know if I want it back. But I'd be happy to let Cas here check me out," she said, biting her lip.

"Sam," Cas said gruffly.

Deana grabbed Cas's hands and placed them at her sides, and stepped a little closer to him. Cas's eyes somehow got wider. "Go one Cas," she said sensually, "Check me out. Make sure it's really me," she bit her lip again and leaned up towards Cas like she was going to kiss him.

"Sam!" Cas shouted, he was panicking.

"Dean! What the hell? Cut it out!" 

Deana raised her eyebrows without visibly shifted her attention from Cas. "I told you, Sammy, it's Deana now," she said, still gazing into Cas's eyes. She let go of Cas's hands but they remained where she'd placed them, right above her hips. Her hands snuck behind Cas's neck and she pulled his head down to kiss him.

Sam just stood in shock for a few seconds while Deana assaulted Cas with various parts of her face.

"I thought you were a lesbian!" Sam exclaimed once he snapped out of it.

Deana separated herself from Cas's face, but did not look away, "I was. Then I saw him."

"Sam!" Cas shouted although most of the damage had been done.

"Dean-"

"Deana!"

"Please leave Cas alone."

Deana rolled her eyes and stepped away from Cas who still hadn't removed his hands from her sides.

"I- I'm going to... get something. Out of my car," Cas stuttered and ran out of the hotel room. Actually ran.

Sam raised his eyebrows and took a step towards Deana, "What the hell was that?" he demanded, "You go from 'Sam I'm a lesbian' to 'Oh, I'll let Cas check me out any time'?"

"I am a celestial being, technically I have no gender," came Cas's voice from outside the door.

"What? I'm a little new to this who chick thing," Deana said, ignoring Cas.

"Dean! Not all chicks are bisexual!"

Deana raised her eyebrows, "Are you sure because-"

"Dude! You're confusing reality with porn again!"

Deana furrowed her brow, looked away, and then looked back at Sam, "Shut up," she said. "So does Cas look different to you?" she asked a little lower.

"Oh, what, you mean since you assaulted him with your face?"

Deana rolled her eyes, "No, I mean before that. I mean, he looks the same, but it's like he's... I don't know, hotter."

Sam's eyes widened in pure annoyance, "And what the hell is up with you? You 'don't want' to get changed back?"

"Yeah," she said innocently, "What's wrong with being a chick? I mean, honestly, this is great. And I don't just mean the anatomy- which, by the way is great. The sex..." she sighed, obviously at a loss for words. "I mean, I can even see how we say we're smarter than dudes," she chuckled. "We really are!"

"We? Dean, you've been a chick for-"

He was cut off as Cas walked through the door.

"I... I've got it," he said softly, holding up his phone which Sam had seen bumping around in his trench coat pocket the first time the angel walked in.

"Great. Now can we talk about how we're going to fix this?" Sam asked.

"There's nothing to fix," Deana snapped. "I am fine with this.

"I don't even know that _you_ are _you_." Sam yelled.

"She's Dean," Cas interjected. 

"Yeah," Deana said, crossing her arms over her chest and leaning towards Sam slightly, "I'm Dean."

Sam rolled his eyes.

"And _I_  am happy as a woman. Cas, come with me, we need to talk," Deana started to walk off. She grabbed Cas's striped tie on her way past him, but let it slip from her fingers as she passed him by. Cas followed anyway, though, back out the door.

Sam sighed and collapsed back on the bed, lying on his back. 

"I should have gone with him," Sam mumbled. "None of this would be happening if I just went with him. How could I be so stupid?" Sam had basically forgotten, at this point, that his ankle had ever been injured in the first place. He stared up at the ceiling and thought about the situation. Actually, what he did, was try to compare the situation to other's he had been in, and find one weirder. He thought about this for a few minutes. All he could think of was sadder. 

"What could Dean possibly have to say to Cas that is taking this long?" Sam said aloud. He stood, grabbed a room key, and exited the room. 

The Impala was still in her parking space, Castiel's Continental beside her, but Cas and Deana were nowhere to be seen. Sam was about to call out their names when he heard the Impala creak. He looked at the car, and noticed it was subtly rocking.

"No," he whispered. "No way," but as he stood in terror, looking through the windshield, Deana sat up in the backseat (perpendicular to the way one would normally sit in a back seat) and threw her head back in what appeared to be pleasure. She was was wearing only her bra that Sam could see, most of her body- and all of Cas's- was blocked by the front seat.

"Six years of sexual tension," Sam mumbled as he turned around and unlocked his room again, "Dean's a girl for one day and they finally hook up."

As Sam fell, once again, onto his bed, he considered what life would be like if Dean really stayed a woman. Would she and Cas be a couple? How would her behavior change? Sam cringed, would he have to buy her tampons? He thought about questions such as these until the door opened again. He looked up, but let his head fall back onto the bed when he saw who it was.

Cas was holding his trench coat and suit jacket, not wearing them, his tie was loose and the top few buttons of his shirt were unbuttoned. His hair had managed to mess itself up even more than usual. Deana was rapidly trying to fix her own hair in front of the mirror, and had, at some point, given up on her flannel. It was probably somewhere in the Impala.

"Sorry about that," Deana said insincerely. "I just had to... do..." she had obviously forgotten her excuse.

"Talk to me," Cas finished. He looked at her, making eye contact with her in the mirror, and smiled fondly. She returned did the same. Sam raised his eyebrows, still looking at the ceiling, not having witnessed the fond smiling.

"Yeah," Deana said, turning back around and making eye contact with the real Cas, not the reflection. Her hands rested on his chest and she stared up into his eyes longingly, as if she had been wanted him for decades, rather than just had him. "Talk to me."

Sam didn't have to look up to know what was happening. "Right," he said, a bit pointlessly since the couple was not paying any attention to him. They were lost in each other's eyes.

Suddenly, Deana took a sharp breath and doubled over.

"Whoa, dude, are you okay?" Sam asked, sitting up abruptly.

"Fuck," she groaned, "Oh my God that is the worst pain I've felt in my enti-" she suddenly covered her mouth with her hand and ran back into the bathroom. She slammed the door shut and Cas, who followed her stopped at the door.

"She's vomiting," Cas informed Sam.

"Oh my God, are you alright?" Sam asked, joining Cas by the door.

"Does this normally happen after intercourse?" Cas demanded, speaking to Sam.

Sam shook his head, "No, Cas. This does not normally happen after sex!"

"Guys?" came a weak voice through the door.

"What?" the two men asked at the same time, crowding the door. Cas tried the handle, but it was locked.

"There's blood."

Cas's eyes widened.

"In your vomit?" Sam asked

"No in..." she was quiet for a moment, "... in my pants."

Cas's eyes got wider still, "Did I hurt you?" he demanded.

Sam scoffed, "No, Cas, she's on her period."

Deana groaned from inside the bathroom.

"Please tell me you made it to the toilet!" Sam said, not really wanting to clean up Dean's vomit as he knew he would have to.

Deana just groaned again.

Sam sighed. "Do I need to run to the store and pick you up some... girl stuff?" he asked.

Rather than answering, Deana opened the bathroom door. She was bent over a little, and clutching her lower abdomen. 

"Cas," she said, "You think you could turn me back now?"


End file.
